Molls, Dolls and Apple Pie
by The Wuzzy
Summary: It's New York, 1925. Dean and Sam are conmen in Lower East Side. When they get caught up in a mafia turf war, Dean is arrested by a cop named Castiel, who frankly, is pretty hot. Can two guys from opposite sides of the tracks navigate their blossoming romance in this dangerous world of flappers, gangsters, incomprehensible slang, and prohibition era apple pie? 1920s AU
1. Chapter 1

'Sammy,' Dean nudged his brother in the arm conspiratorially, and got a scowl for his trouble, 'See the gams on that bim?'

Sam groaned and passed a meathook over his ridiculously long hair, glancing over to where the canary in question was belting out the St. Louis Blues. As she swayed in time with the rhythm, the fringe of the doll's spangled dress caught the low lighting of the speakeasy, and sent glittering patterns across the faces of the enraptured customers.

'That's Ruby, Dean,' Sam explained. 'She may be a sheba, but I'm warning you, she's Crowley's blue serge and a real bearcat.'

'Alright, wiseguy,' Dean muttered, sending a dark look at the Brit in question, who was plucking away at a double bass.

Wait a minute – that was hinky. Where'd the rest of the regular band go?

Dean didn't recognise any of the other players, and judging by Crowley's annoyed expression, neither did he. This new bunch was pretty poor, sending each other shifty looks in between tunes, and holding their instruments awkwardly. The palooka at the piano had not only forgotten to take off his trench coat but was glaring at the keyboard as though it was going to attack him, pale fingers bashing out a discordant tune.

Dean winced, making a mental note to tell Bobby that the next time he got a little overenthusiastic and fired the whole band, he should try and hire actual _musicians._ Even _if_ one of the alternatives was a sheik with some serious cheekbones.

Dean's eyes widened. Hold up - did he just think that about a guy?

Sam shifted uncomfortably, and tugged at his tie. 'Dean, I don't think we should be partners any more.'

Dean turned back to his brother, grateful for the chance to tear away his gaze. 'What's eating you? You want to go solo?'

'No,' Sam passed his trilby between his hands, 'I want out.'

Dean stared at his brother cluelessly. 'Don't be sill, killjoy, we're Winchesters. This is what we do – scamming suckers, glauming things. You know, the family business.'

'Exactly,' Sam's wide forehead creased into a frown, 'We're nothing but a coupla red hot Johnson brothers.'

'Tell it to Sweeney,' Dean shrugged, 'Everybody's gotta earn their spondulicks somehow.'

'I guess,' said Sam uneasily.

'Now you're on the trolley,' Dean held up his giggle water, 'No point beating our gums about it.'

At that moment the doors slammed open, and what looked like half of Shaky Zach Ricci's chopper squad entered the joint. They fanned out around the side of the room, hands lifting the sides of their floggers just enough to make it clear they were packing heat. The band ground to a squeaky halt, Ruby's voice quavering nervously to a stop.

'Aw, shucks,' said Dean. 'It's the mob!'

Things were clearly about to go south. In one smooth movement, Dean slid down behind their table, dragging a confused Sam with him. Through chair legs Dean saw a pair of spats click across the polished floor, and he tilted his head upwards to see the pasty, balding head of Zachariah himself come swaggering in. Bobby had appeared out of a side room to block his way forward, arms folded and expression making it clear he wouldn't be taking any wooden nickels.

'Zach,' Bobby growled, 'you know I don't like it when you bring your boys into my bar. This is neutral turf.'

'Ah, fuggedaboudit,' drawled Zach, clapping one hand on Bobby's shoulder with a smile that didn't reach his piggy little eyes. 'We're just here to take the Winchesters for a ride.'

'Hot socks, Dean,' Sam muttered, as Dean pressed his hat to his head and went for his mohaska, 'What the hell did you do this time?'

'Huh?' frowned Dean, 'Why am I always left holding the bag?'

Sam gave him such a bitch face that Dean shrugged and realised he really couldn't argue.

'I'm sorry, Zach,' said Bobby, 'But I haven't seen those boys since Tuesday. You should look elsewhere, or I'll have to give you the bum's rush.'

Zach's eyes bulged, and his face flushed momentarily purple. Then he began to laugh, palms raised in a gesture of mock surrender. He flicked a finger, and there was the unmistakeable sound of hammers being cocked from around the room. The customers who hadn't already beat it began to get a wiggle on right about then.

Bobby sighed, and gave an apologetic shrug in Dean and Sam's direction. 'They're under that table.'

'You've got to be _gassing_ me,' snarled Dean.

'Now we're really behind the eight ball,' agreed Sam.

In synchronisation the brothers rose to their feet, doffing their hats, Dean's most charming grin plastered all over his face. 'Well, whaddya know, if it isn't my old bo Shaky. Father Time, fancy tipping a few?'

Zach's face went slightly purple. 'Dean Winchester,' he spat, 'Dry up, weasel. You screwed up our box job caper - '

'Who, me?' Dean glanced around, as though he might be referring to someone else.

'Now, let's all just stay calm and talk this through sensibly, okay?' said Sam.

Zach wasn't having it. 'Your brother tooted the wrong ringer and breezed off with the heavy sugar - '

'I got cold feet and needed some Jack,' Dean shrugged.

'And do you know what?' Zach was shaking a podgy finger. 'I woulda let you off for all that. Hell, I even thought it was funny.' His face twisted. 'If you hadn't then gone and nookied my dame in the back of your struggle buggy.'

'Dean,' Sam spluttered.

'Oh. That,' said Dean. 'Well, she was a hotsy-totsy with a really nice pair of- '

At that second the torpedoes pulled out their bean-shooters, and let loose with the Chicago lightning. Dean and Sam threw themselves to the floor as flour lovers, flappers and bug-eyed Bettys started shrieking. Suddenly, the jazz band bar Crowley jumped up, throwing aside their instruments and drawing out roscoes. The size of the piano man's chopper – no _wonder _he'd been wearing the trench. It was the cops!

'Somebody's dropped a dime,' Dean yelled over the increasing noise of burning powder as the fuzz joined in the showdown and got Zach's triggermen surrounded, 'The buttons are here!'

'And how!' Sam roared in reply. 'Zach's been flim-flammed, and now we're gonna get zotzed in the cross-fire!'

Just like that, there was silence.

'Alright!' called the piano-man, in a voice made of gravel. He was standing over a cowering Zach and wielding a gat. 'All you trouble boys better grab a little air. I'm the law… and I'm heeled.'

The bulls surveyed calmly as, slowly, the goons all laid down their pieces. Meanwhile Dean began to shift slowly towards the exit.

'You've been pinched, Shaky Zach Ricci,' growled the trench coat, drawing out his buzzer, 'The name's Castiel Novak, NYPD. I'm escorting you and your Jobbies back to the hoosegow.'

Suddenly, the cop's ridiculously blue eyes locked onto Dean's, and he froze, feeling his breath hitch.

'And that includes _you_, Dean Winchester.'

Dean swallowed. Well, today was just turning out swell.


	2. Chapter 2

**This whole story is dedicated to W1ccan, for giving me the awesome prompt.**

**oOoOoOoOoOo**

Dean was handcuffed to the table of a holding room.

After the first ten minutes of snapping a cap to be let out (no reply) and the next twenty cussing Detective Inspector Novak's momma (still no reply) he had spent fifteen trying to cheese it out of the nippers (this failed).

Dean refused to give in to the urge to pine after a chiv. If there was one thing he was good at, it was spitting his way out of a jam. Take that time Madhouse Micky had mistaken him for one of Lucio 'Loco' Angeli's hatchet men, for example. Yeah, so he'd taken several of Mama Harvelli's apple pies to the pan before he'd finally managed to sing his way out (Dean winced in memory of all the wasted pastry) but he _had_ hit all sixes eventually.

Thing was, he'd never tried to make a clean sneak with one of the fuzz before.

'Get me a lawyer,' Dean said, the moment he heard the door open behind him. His words died in his throat as the flattie in the trench crossed round into his field of vision, and DI Novak fixed him with a stare. Blue eyes stood out against pale skin and dark hair so casually messy that Dean bet the egg spent hours fixing it in front of a mirror.

'Dean Winchester,' Novak's voice was rocks on more rocks, 'looks like you're in the cooler.'

'What's your beef, gravelly? You on three decks of luckies a day?' Dean attempted to lean back casually in his chair, but was jerked to a stop. Horsefeathers - he'd forgotten his wrists were still manacled to the table.

Castiel simply narrowed his peepers slightly in response and then cocked his noodle, which gave Dean the heebie-jeebies.

'You think I'm on gaspers? I'm a John. The voice comes with the job, sucker.'

Dean swallowed. For some reason when Castiel spoke he found himself getting a little warm around the collar.

'You don't really look like one of the bulls.' The gumshoe didn't, with his loose tie and five o'clock shadow, and to be honest, Dean didn't think elephant ears were supposed to be this keen. 'You're too much of a looker.'

Hold on. Did he just spill that?

He did _not_ just spill that.

Castiel leaned over towards Dean, hands braced on the table. 'Cut the spooning, line, bank's closed.'

Dean reckoned he must have spilled it.

'Alright, Cas,' he drawled, 'This grilling's been swell, but I'm a busy guy. I'm done with the bull session,' Novak's poker face twitched slightly at the abbreviation of his name, 'so if we're done bumping gums…?' Dean held up his metal bound wrists pointedly.

Castiel sighed, then reached inside his trench to pull out file of papers. Dean's file. It was so full he almost felt proud.

'Three counts of Chinese squeezing, two soup jobs,' Castiel said, flicking lazily through the file, 'repeated chiselling, buncoing, and gloaming orchids worth a whole load of cabbage. Oh, and you were pinched in a juice joint with bootleg.' He slammed the papers down in front of Dean, never once breaking eye contact. 'You're not going anywhere, hombre.'

Jeepers, did the guy never blink? Dean swallowed and glanced down at the file, to see _that _mugshot from Little Rock prison taped on the front.

'You can't keep me, bluenose ,' he smirked, 'You've got no proof.'

'But we _do_ have your machine,' Castiel was smirking right back.

Applesauce. Dean kept _everything_ in the boot of his boiler.

'Now we're on the level,' said Castiel, leaning back and folding his arms. Dean licked his lip, stalling for time. Castiel had the bulge, and he knew it.

'Pass the ameche,' Dean said eventually, 'I need to get on the horn.'

'Be my guest.' Castiel gestured with one hand at the telephone which sat to one side on the table top.

'So you gonna undo me, Mrs. Grundy?'

'No,' said Castiel. 'Tell me the number and I'll dial.'

'It's lucky you're a sheik, Cas,' Dean muttered to himself. Of course, Castiel heard him.

'Close your head,' he said, voice entirely matter of fact, 'or I'll fill you full of lead.'

Dean bit down on his frustration, and told him the number. Cas slowly spun the dial with one finger, then raised the receiver to his own ear.

'Hey, what- '

Castiel held up a finger, and Dean trailed off.

'Sam Winchester? This is Castiel Novak… yes, he's with me.' He regarded Dean with an expression that could only be described as smug. 'Your patsy brother's hitting on all eight, actually. No, but you can chin.'

Castiel shoved the receiver between Dean's cheek and shoulder. 'Two minutes.'

'Dean? Where'd you lam off to?' Sam's concerned voice crackled in his ear. 'Is everything Jake? And who's this Castiel you're with? Is he another gigolo? What have I told you about skating around like some drugstore cowboy - '

'I'm at the clubhouse, you dumb mug,' Dean interrupted.

'Say _what_?'

'I'm in the can, Sammy,' Dean hissed, 'the piano man nailed me, and I'm sitting here on the rap like a fish. Now are you gonna get one of your shyster pals to help me blow this joint, before I end up in the bing doing a three-spot?'

Castiel was drumming his fingers slowly on the tabletop beside him. Dean shifted, he was trying to have a barber, and the bruno clearly hadn't heard of personal space.

'Sorry, but I need to see a man about a dog,' Sam said, sounding mildly tearful, 'After you left, Crowley got fogged and they took him away in the meat wagon. Bobby reckons he's hit the big one and he's lying in his wooden kimono, so we're heading down to Mama Harvelli's for the gigglejuice to get fried to the hat.'

'Crowley wasn't your pal,' Dean said incredulously, 'He kissed you on the schnozzle, remember?'

'He was just some poor boob, and now he's been pooped' Sam hiccupped, 'Plus… Ruby needs a shoulder to cry on.'

Dean ground his teeth. He could picture them all getting out on the roof without him, Ash and Jo racking up dead soldiers, while Gordon downed tiger milk and Ellen dished out endless rounds of pie. But since when was _Sam _into Ruby?

'Don't wait up,' Dean said sarcastically, 'but you better get your _own_ sawbucks to pay for the hooch.'

'That's ducky then,' Sam sighed, 'I guess I'll go get splifficated.'

'Hold up,' said Dean, 'I'm still stuck here - '

But the other end of the line had already gone dead.

'I need a hair of the dog,' Dean groaned, as Castiel replaced the blower.

At that moment the door slammed open, and Dean twisted around to see some hard boiled jobbie enter the room. 'The jalopey is empty,' the big six said. 'Someone cleaned out the evidence.'

Thank god for Sammy's quick thinking. 'Looks like you're going to have to let me go, Cas,' Dean said, and he couldn't keep back another smirk.

Castiel stared at him, face impassive, but Dean was rewarded by a slight tightening of his lips. Strike one. The other pill exited, and Cas reached inside his coat again for the key to Dean's bracelets. Standing way closer than necessary, he took Dean's wrists in his hands to undo the nippers.

'Have a drink with me,' Dean found himself saying.

Castiel's hand round the key froze in mid turn. 'Maybe you haven't crabbed, but I'm with the heat.'

Dean spread his hands. 'And I'm a law abiding citizen. You don't know from nothing, remember?'

'Give me one good reason why I should put up with you barbering on all evening.' Castiel sounded sore, but from the glint in his eye Dean reckoned he'd slayed him.

Time to dial up the Winchester charm to eleven.

He raised his eyebrows at Castiel. 'Do you really need a reason?'

Castiel ranked Dean, and wet his top lip thoughtfully. 'I guess I could nibble one.'

'Copacetic,' Dean smiled.

'Not some hash house,' said Cas, 'It'd better be spiffy.'

'I know just the dive,' said Dean, and he couldn't wait to see Mama Harvelli's map when he asked her to put on the Ritz for a button.

'And you're getting the rhino.'

'Cas,' said Dean, standing up and clapping a mitt on his shoulder, 'You're the bees knees.'

Then all the wind was knocked out of him as Castiel slammed him into the wall, fists tight around the lapels of his flogger, and face inches from Dean's.

'One final condition,' he growled. 'Call me that monicker again, and I'll paste you in the beezer. Savvy?'

'Cas, you're the…cat's pajamas?' Dean hazarded.

Castiel raised an eyebrow dangerously.

'Okay, okay,' Dean raised his hands in surrender, 'No more nicknames.'

Castiel nodded, satisfied, but didn't seem to have any intention of moving. They were still squashed together against the wall, and Dean couldn't help his gaze flicking down to Castiel's mouth. Cas seemed to be struggling to breath smooth too.

Yep, they were totally goofy for eachother. Well, at least then tonight was going to be a whoopee not an oilcan.

'Cash or check?' Dean risked.

Castiel brought his lips forward to Dean's, and Dean knew he'd turned into a tomato when felt himself go all jingle-brained.

'Cash,' said Cas, pulling away. 'Now scram.'

'Pipe you later,' said Dean, grinning like some dumb Dora on prom night. He scrammed.

**oOoOoOoOoOo**

**That's all, folks! I hope you enjoyed it. This was my first ever Destiel fic, and my first ever AU – I actually had an awful lot of fun. Cripes did adding in the slang take a long time. :P **


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